This compound belongs to the class of organic compounds known as halobenzoic acids. These are benzoic acids carrying a halogen atom on the benzene ring.
External Descriptors
Not available
1. Djoumbou Feunang Y, Eisner R, Knox C, Chepelev L, Hastings J, Owen G, Fahy E, Steinbeck C, Subramanian S, Bolton E, Greiner R, and Wishart DS. ClassyFire: Automated Chemical Classification With A Comprehensive, Computable Taxonomy. Journal of Cheminformatics, 2016, 8:61.
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Recensioni
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Application Protocols
Not applicable. No validated bioassay protocols (WB, IHC, IF, FC) are associated with this small-molecule building block.
General lab usage examples (non-validated, literature-based)
Prepare 100 mM stock in anhydrous DMSO for combinatorial coupling screens.
For stepwise coupling: conduct iodo-selective Suzuki first, isolate, then perform chloro activation/coupling; finalize by amidation/esterification of the acid.
Refer to published synthetic procedures for detailed, substrate-specific protocols.
Biological Roles
Product Data (item-specific)
No biological role or activity is specified. For research use only.
Literature/general context
2-Chloro-6-iodobenzoic acid is a synthetic halogenated benzoic acid used as an intermediate; it is not known as a natural metabolite or cofactor.
Benzoic acid framework is common in biochemistry, but heavy halogenation (Cl, I) generally reduces biological turnover and increases hydrophobicity, making such compounds more typical as synthetic handles than as bioactive metabolites.
Potential lab uses include preparation of radiolabel surrogates (e.g., exchange at iodine with radioiodine in different scaffolds) or as a hapten precursor in immunochemistry after conversion to amide/ester, though no application is specified for this item.
No clinical or therapeutic claims are made or implied. Use is limited to laboratory research.
Buffer Applications
Not typically applicable.
As a hydrophobic aromatic carboxylic acid, this compound is not used as a buffering agent. For solution preparation, it may be dissolved in organic solvents (DMSO/DMF) or converted to its sodium salt for aqueous studies, but dedicated biological buffers (e.g., phosphate, HEPES) should be used for pH control.
Green Alternatives
Context
This reagent is a halogenated aromatic acid used primarily as a building block. The “green” discussion centers on solvent/catalyst choices and step economy rather than a direct substitute for the molecule itself.
Greener process considerations (literature/general)
Solvents: Replace DMF/dioxane/CH2Cl2 with 2-MeTHF, CPME, ethyl acetate, or water/ethanol mixtures when compatible. Consider propylene carbonate or Cyrene for polar-aprotic needs.
Catalysis: Employ ligand-optimized Pd at low loadings or Ni-catalysis for cross-couplings; consider photoredox/Ni dual catalysis for decarboxylative couplings.
Step economy: Use chemoselectivity of Ar–I vs Ar–Cl to minimize protecting steps; sequence couplings to avoid additional halogenation steps.
Energy: Microwave or flow processing can reduce reaction time/energy footprint.
Comparison snapshot (general guidance)
Conventional vs greener setups:
Cross-coupling solvent: Dioxane/DMF vs 2-MeTHF/EtOH–H2O
Base: K2CO3/K3PO4 vs aqueous carbonate in biphasic systems
Workup: Chlorinated extraction vs EtOAc or MTBE
Trade-offs
Greener solvents may reduce substrate solubility; adjust temperature or use co-solvent.
Ni-catalysis can be more substrate-sensitive; optimization required.
Item-specific environmental data are not provided; consult your EHS team and SDS for waste classification and treatment.
Pharmaceutical Uses
Product Data (item-specific)
No pharmacopeial grade or excipient designation is provided. For research use only.
Literature/general context
Halogenated benzoic acids like this serve as synthetic intermediates in medicinal chemistry programs, enabling modular introduction of substituents via selective cross-coupling at Ar–I followed by diversification at Ar–Cl and the acid function (amide/ester libraries).
Formulation/excipient use is not typical for this structure due to hydrophobicity and lack of established safety profile as an additive.
When used in drug discovery workflows, stock solutions are commonly prepared in DMSO for screening cascades after derivatization; the parent acid itself is generally a building block rather than a formulated entity.
Physical Properties
Product Data (item-specific)
Appearance: Not specified for this item; refer to CoA/Spec Sheet.
Molecular Formula: Not specified for this item; refer to CoA/Spec Sheet.
Molecular Weight: Not specified for this item; refer to CoA/Spec Sheet.
Literature/general values (for context; not specifications for this lot)
Physical state: Typically a crystalline solid for halogenated benzoic acids of this type.
Melting point: Often in the 180–230 °C range for ortho-dihalobenzoic acids (literature, compound-specific values vary by purity and polymorph).
Boiling point: Not practical (decomposes before boiling at 1 atm; literature trend for benzoic acids).
Solubility: Low in water at neutral pH; readily soluble in polar aprotic solvents (DMSO, DMF, NMP). Soluble in alcohols upon heating. Forms water-soluble salts with bases (e.g., NaHCO3, NaOH).
pKa (carboxylic acid): Benzoic acids typically pKa ~4.0–4.5; ortho halogenation can modestly increase acidity (literature trend; specific pKa for this isomer not verified here).
LogP: Aromatic carboxylic acids with two halogens generally exhibit moderate hydrophobicity (literature expectation: logP in the 2–3.5 range in neutral form; decreases upon ionization).
Refractive index/density: Not applicable for solids (nD) and item-specific density not verified.
Notes
Use the item’s CoA for definitive property values (mp, purity, appearance). Values above are general literature guidance only.
Quality and Grades
Product Data (item-specific)
Grade/Purity: Not specified for this item; refer to CoA/Spec Sheet.
Interpreting grade (general guidance)
If supplied as “analytical” or “≥98%,” typical implications include suitability for synthesis and analytical development. HPLC-grade descriptors usually refer to low UV-absorbing impurities; for solids like this, purity is usually established by NMR/GC/LC and sometimes titration for acid content.
Stabilizers: None indicated for this item. The listing notes argon-charged storage, suggesting attention to long-term stability (minimizing oxidative or light-initiated changes), though no specific degradation pathways are specified here.
CoA checkpoints: Confirm identity (1H/13C NMR consistent with ortho-dihalobenzoic acid), purity (% area by HPLC/GC), residual solvents, water content (Karl Fischer) if applicable, and halogen distribution (HRMS).
Practical tips
For cross-coupling use, trace metal impurities and halide integrity can impact reactivity; consider small test couplings to benchmark performance.
If LC methods are UV-based, ensure baseline separation from positional isomers (e.g., 2-chloro-4-iodo- vs 2-chloro-6-iodobenzoic acid).
Reaction and Applications
General reactivity (literature)
Orthogonal aryl halides: The aryl iodide typically undergoes oxidative addition more readily than the aryl chloride, enabling chemoselective cross-coupling at C–I while preserving C–Cl for subsequent elaboration.
Carboxylic acid handle: Amenable to esterification, amidation (via DCC/EDC or acid chloride), and decarboxylative transformations under photoredox or transition-metal catalysis.
Representative applications
Suzuki–Miyaura coupling (Ar–I): Pd(0) catalysts (e.g., Pd(PPh3)4), bases like K2CO3/K3PO4, solvents such as toluene/dioxane/H2O at 60–100 °C to introduce (hetero)aryl groups, leaving Ar–Cl intact for a second coupling.
Sonogashira coupling (Ar–I): PdCl2(PPh3)2/CuI with amine base (Et3N, DIPEA) in THF/DMF for alkynylation; subsequent hydrogenation/functionalization possible.
Buchwald–Hartwig amination (on Ar–I): Ligands (e.g., BINAP, XPhos) with Pd sources to install anilines while retaining the C–Cl.
Nucleophilic aromatic substitution (Ar–Cl): Under strong conditions (e.g., with electron-withdrawing activation), Ar–Cl can be displaced; otherwise employ Pd-catalyzed coupling to functionalize C–Cl after the iodide step.
Acid derivatives: Convert to acid chloride (SOCl2, oxalyl chloride; catalytic DMF) for subsequent amide/ester formation; peptide-coupling reagents (EDC·HCl/HOBt or HATU) also effective.
Decarboxylative couplings: Under photoredox or Ag/Pd-mediated conditions, the acid (as NHPI ester) serves as a radical precursor for C–C or C–heteroatom formation.
Practical tips
Maintain anhydrous, oxygen-minimized conditions for cross-couplings; the product listing’s argon charge aligns with best practice.
Ortho substitution may slightly reduce rates due to sterics; ligand/catalyst choice can restore activity.
Reaction Conditions
General literature guidance (not item-specific specifications)
Suzuki–Miyaura (Ar–I): Pd(PPh3)4 (1–2 mol%), K2CO3 or K3PO4 (2–3 equiv), 1,4-dioxane/H2O or toluene/H2O, 60–100 °C, 2–12 h. For steric hindrance, use SPhos/XPhos ligands or Pd-PEPPSI-type catalysts.
Sonogashira (Ar–I): PdCl2(PPh3)2 (1–2 mol%), CuI (5–10 mol%), terminal alkyne (1.2–1.5 equiv), Et3N or DIPEA, THF/DMF, rt–60 °C, 2–8 h. Copper-free protocols (Pd/XPhos, amine solvent) help suppress Glaser coupling.
Buchwald–Hartwig (Ar–I first; later Ar–Cl): Pd2(dba)3 (1 mol% Pd), biaryl phosphine ligand (e.g., XPhos, BrettPhos), NaOtBu or Cs2CO3, toluene or tAmOH, 80–110 °C, 6–18 h. For Ar–Cl activation, stronger ligands (BrettPhos, RuPhos) and higher temperature are typical.
Acid chloride formation: SOCl2 (2–5 equiv), catalytic DMF, CH2Cl2 or toluene, 0–reflux, 1–3 h; subsequent amidation with amines and base (Et3N, pyridine) at 0–25 °C.
Decarboxylative couplings: As NHPI ester with photocatalyst (Ir/Ru or organic), Ni co-catalyst, blue LEDs, MeCN or DMAc, rt–40 °C, 4–16 h.
Practical notes
Ortho sterics can slow reactions; increasing catalyst loading or switching to bulky/electron-rich ligands often restores rates.
Maintain inert atmosphere (argon) as per product handling guidance; dry solvents and bases are important for reproducibility.
Safety and Handling
Product Data (item-specific)
GHS Classification: Not specified for this item; refer to SDS.
Signal word / H-statements / Pictograms: Not specified for this item; refer to SDS.
Storage conditions: Protected from light; Room temperature; Argon charged (store tightly closed under inert atmosphere).
Shipping: Shipped under normal conditions (per listing).
General safety considerations (literature/experience; defer to SDS for authoritative guidance)
Likely hazards: Irritation to skin/eyes/respiratory tract typical of aromatic acids; halogenated aromatics may be hazardous to the aquatic environment. Avoid dust formation and inhalation.
Incompatibilities: Strong bases (will form salts; exotherm possible on neutralization), strong oxidizers or reducers under forcing conditions, and reactive metals. Avoid prolonged contact with light and moisture which may affect stability over time.
Peroxide formation: Not applicable (non-ether). No specific self-reactive hazards expected under recommended storage.
PPE: Lab coat, nitrile gloves, splash goggles. Handle in a fume hood to avoid inhalation of dust or vapors during reactions (e.g., acid chloride formation).
First aid (overview): If inhaled—fresh air; seek medical attention if symptoms persist. Skin/eye contact—rinse with water for several minutes; remove contaminated clothing. If ingested—rinse mouth; do not induce vomiting; seek medical attention.
Spill/cleanup: Avoid dust, collect mechanically, place in appropriate waste. Prevent release to the environment.
Always consult the product SDS for definitive hazard classification and response.
Solvent Selection
Polarity/miscibility profile (literature/general)
The neutral acid is poorly soluble in water but dissolves in polar aprotic solvents (DMSO, DMF, NMP) and in hot alcohols. Deprotonated carboxylate is water-soluble.
For cross-coupling at the aryl iodide: toluene, dioxane, THF, DMAc, or DMF are common. Aqueous co-solvents (H2O, EtOH) may be used with bases like K2CO3 or K3PO4.
Selection guidance by task
Stock solutions: DMSO or DMF (10–100 mM typical) for HTS or small-scale reactions.
Esterification/acid chloride formation: Use dry chlorinated solvents (CH2Cl2) or toluene; ensure removal of residual DMF if used as catalyst for SOCl2 reactions.
Salt formation/extractions: Adjust pH to >8 to extract as water-soluble carboxylate; re-acidify to precipitate the free acid.
Comparison (general)
DMSO vs DMF: DMSO offers higher solubility and is less volatile; DMF is easier to remove but can form dimethylamine upon aging. 1,4-Dioxane or 2-MeTHF can provide good coupling performance with improved workup volatility.
Notes
Item-specific solubilities are not provided; verify experimentally at process-relevant concentrations.
Storage and Reconstitution
Product Data (item-specific)
Storage conditions: Protected from light; Room temperature; Argon charged.
Shipped in: Normal conditions.
Practical guidance (general)
Keep container tightly closed under inert gas to minimize oxidative or photochemical changes. Store in a dry place; use a desiccator if ambient humidity is high.
Reconstitution/solutions: For stock solutions, use anhydrous DMSO or DMF. Filter if particulates are present. Record concentration and date; for long-term solution storage, aliquot and keep under inert atmosphere at low temperature (e.g., −20 °C) to minimize hydrolysis of derived acid chlorides or activated esters.
Freeze–thaw: For solutions, avoid repeated freeze–thaw by aliquoting. The neat solid generally tolerates room temperature storage per listing.
Stability testing
Item-specific stability data are not provided; check recovery/purity by HPLC or NMR after storage for critical applications.
Always follow the label and CoA/SDS for definitive handling instructions.
Research Use Only.
Structure and Identity
Product Data (item-specific)
SKU: C190615
Product name: 2-Chloro-6-iodobenzoic acid
CAS: 13420-63-8
PubChem CID: 13399374
InChIKey: 184998 (as provided)
SMILES: Not specified for this item; refer to CoA/Spec Sheet.
Literature/computed (general reference; not item-specific specs)
Expected molecular formula (literature): C7H4ClIO2
Calculated molecular weight (literature): ~286.46 g/mol (using I = 126.90, Cl = 35.45). Note: Some databases may list ~286–287 g/mol depending on atomic weight basis.
Structural features (descriptive): A benzoic acid core (carboxylic acid at C1) bearing ortho substituents chlorine at C2 and iodine at C6 (1,2,6-substitution pattern relative to CO2H). Contains one carboxyl functional group (–CO2H) and two aryl carbon–halogen bonds (Ar–Cl and Ar–I). Planar aromatic ring; no stereocenters.
2D structure in words (general): A benzene ring with a carboxylic acid group; moving clockwise from the carboxyl carbon as position 1, chlorine is at position 2 (ortho), hydrogen at positions 3–5, and iodine at position 6 (ortho), yielding a dihalogenated benzoic acid suitable for orthogonal aryl–iodide chemoselectivity.
Synthetic Utility
Functional group handles (literature)
Carboxylic acid: Convert to acid chlorides, esters, amides; engage in coupling via EDC/HATU; decarboxylative strategies after activation (e.g., NHPI esters).
Aryl iodide: High reactivity in oxidative addition—ideal for first-stage cross-couplings (Suzuki, Sonogashira, Heck, Buchwald–Hartwig) with chemoselectivity over Ar–Cl.
Aryl chloride: Reserved for second-stage couplings or SNAr under activating conditions; can be leveraged for late-stage diversification.
Strategic value
Orthogonal handles enable concise two-dimensional SAR expansion around a benzoic core: first functionalize C–I, then C–Cl, independently of acid derivatization.
Ortho substitution can enable directed metalation adjacent to the carboxyl (in other isomers), but for this substrate, sterics primarily influence coupling ligands and bases.
Typical transformations (examples)
Iodo-selective Suzuki to install heteroaryl boronates (e.g., pyridyl), followed by chloro-selective Buchwald amination to form anilides, and final amidation of the acid—three orthogonal steps from one scaffold.
Conversion to mixed anhydrides for Curtius or Schmidt rearrangements to access anilides/isocyanates (advanced applications with care).
Notes
Sequence planning is key: exploit the innate reactivity order I >> Br > Cl to minimize protecting steps and maximize yield across telescoped sequences.
Target Specificity
Not applicable. This product is a small-molecule building block, not a biological targeting reagent. No antigen/epitope, species reactivity, clone, or isotype information applies.
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